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Sigma-Aldrich

PyAOP

for peptide synthesis, Novabiochem®

Synonym(s):

PyAOP, (7-Azabenzotriazol-1-yloxy)trispyrrolidinophosphonium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C17H27F6N7OP2
CAS Number:
156311-83-0
Molecular Weight:
521.38
MDL number:
MFCD03703417
UNSPSC Code:
12352101
NACRES:
NA.22

product name

PyAOP, Novabiochem®

Quality Level

200

product line

Novabiochem®

form

powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

storage temp.

15-25°C

InChI

1S/C17H27N7OP.F6P/c1-2-11-21(10-1)26(22-12-3-4-13-22,23-14-5-6-15-23)25-24-17-16(19-20-24)8-7-9-18-17;1-7(2,3,4,5)6/h7-9H,1-6,10-15H2;/q+1;-1

InChI key

CBZAHNDHLWAZQC-UHFFFAOYSA-N

Related Categories

General description

PyAOP is an extremely effective coupling reagent that mediates amide bond formation with the efficiency of HATU but without the risk of guanidine formation, making it the reagent of choice for peptide cyclization.

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references:
[1] F. Albericio, et al. (1997) Tetrahedron Lett., 38, 4853.

Application

PyAOP can be used as a coupling reagent:
  • In the synthesis of N,N′-substituted acylguanidines by solid-phase peptide synthesis.
  • To facilitate the formation of peptide bonds during the synthesis of cyclic peptide hybrids.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Solid-phase synthesis of N, N?-substituted acylguanidines
Dodd DS and Zhao Y
Tetrahedron Letters, 42, 1259-1262 (2001)
Synthesis of cyclic peptide hybrids with amino acid and nucleobase side-chains
Planas M, et al.
Tetrahedron Letters, 41, 4097-4100 (2000)
On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis
F. Albericio, et al.
Tetrahedron Letters, 38, 4853-4853 (1997)

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